By the 1910s, the United States had firmly established state-run institutions to carryout its brand of colonialism in the Philippines, “benevolent assimilation.” The new colonial state promised to uplift Filipinos and bring modernity, industrialization, and wealth. However, an examination of labor in colonial state-run industrial schools and prisons and specifically in the sector of embroidery production, one of the most profitable exports, reveals a troubling story of racialized and gendered exploitation. These institutions appeared as exemplars of reform and the uplift, granting Filipino women and girls the education and skills to participate in an advancing and industrializing society. In actuality, prisons and schools provided a controlled environment where educating “pupil workers” and women prisoners became a way to create a vulnerable and exploitable workforce for the profit of the colonial state and American investors. By linking embroidery and labor to colonial education and prison systems, this paper questions the “benefits” of American colonialism and explores the hidden cost of uplift.